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- Heeled Ankle Boots
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High-Heel Ankle Boots
ShopSimon (formerly Shop Premium Outlets) High-Heel Ankle Boots
ShopSimon (formerly Shop Premium Outlets) High-Heel Ankle Boots
-27%
David Tate
Womens David Tate Alison Boot Black Leather Almond Toe Block Heel JOBB171
$159.95
$220.00
ShopSimon
-15%
Vionic
Womens Nella Ankle Boot In Camel Brown
$120.00
$142.00
ShopSimon
-24%
Naturalizer
Womens Naturalizer Bay Boots US Chocolate Leather Waterproof Booties GAL628 Brown
$175.00
$230.00
ShopSimon
-14%
Marc Fisher
Womens Marc Fisher Dyvine Boots Black Faux Suede Block Heel Bootie ZOGG2226
$99.00
$115.00
ShopSimon
-58%
David Tate
Womens Ania Leather Stacked Heel Ankle Boots In Black
$72.00
$173.00
ShopSimon
-22%
Born
Womens Kimmie Boots In Taupe Gray
$113.00
$144.00
ShopSimon
-24%
Vionic
Womens Vionic Truckee J0721L1001 Black Leather Ankle Boots ZOGG1349
$189.99
$250.00
ShopSimon
-19%
London Rag
kaira metallic accent heel high ankle boots Black
$69.00
$85.49
ShopSimon
-51%
Lucky Brand
Womens Jabilo Snake Ankle Boots In Natural Jame Snake Gray
$68.00
$139.00
ShopSimon
-47%
Xti
Carmela CollectionWomens Leather Booties By XTI Black
$87.95
$165.00
ShopSimon
-27%
Journee Collection
Womens Journee Collection Adria Bootie Black Faux Leather Ankle Boots GAL1207
$109.99
$150.00
ShopSimon
-46%
Journee Collection
Collection Womens Tru Comfort Foam Wide Width Noralinn Booties Brown
$69.99
$129.99
ShopSimon
-13%
Xti
Womens Ankle Booties In Fuxia
$111.00
$128.00
ShopSimon
-16%
Dolce Vita
Womens Dolce Vita Henla Boots Black Leather Block Heel Ankle Bootie RHS6621
$160.00
$190.00
ShopSimon
-46%
Journee Collection
Collection Womens Tru Comfort Foam Wide Width Noralinn Booties Orange
$69.99
$129.99
ShopSimon
-75%
Alexander Wang
Kori Cutout Ankle Boots In Black Leather
$196.00
$789.00
ShopSimon
-15%
Guess
Womens GBG Los Angeles Aheela Boot Black Wedge Heel Ankle Bootie JOBB2072
$50.00
$58.93
ShopSimon
-50%
L.k. Bennett
Margaux Ankle Boots Beige
$325.00
$650.00
ShopSimon
-21%
Staud
Womens Wally Ankle Boot In Dune Beige
$313.00
$395.00
ShopSimon
-20%
Gabor
Womens Almond Toe Block Heel Bootie In Kiesel Beige
$206.00
$259.00
ShopSimon
-2%
Xti
Womens 144277 Heeled Booties In Beige
$126.00
$128.00
ShopSimon
-3%
Xti
Womens Refresh 173015 Booties In Beige
$124.00
$128.00
ShopSimon
-23%
Miz Mooz
Womens Carlitos Boots In Dust Brown
$205.00
$265.00
ShopSimon
-73%
Marsèll
BROWN FUNGHETTO CALF/DEER LEATHER ANKLE BOOTS
$206.00
$770.00
ShopSimon
-36%
Xti
Womens Suede Ankle Booties By XTI Brown
$73.95
$115.99
ShopSimon
-22%
Anne Klein
Moore Boots Womens Beige Almond Toe Block Heel Booties LION588
$109.65
$140.00
ShopSimon
-22%
Anne Klein
Moore Boots Womens Beige Almond Toe Block Heel Booties LION593
$109.65
$140.00
ShopSimon
-26%
Homers
Sharon Heeled Ankle Boot In Dark Green
$332.00
$449.00
ShopSimon
-23%
Eric Michael
Womens Liza Ankle Boot In Gold Metallic
$222.00
$288.00
ShopSimon
-26%
Eric Michael
Womens Trento Booties In Copper Gold
$312.00
$421.00
ShopSimon
-52%
Michael Kors
Selina Leopard Print Calf Hair Ankle Boot Brown
$107.00
$225.00
ShopSimon
-69%
Stuart Weitzman
Renegade Pointed-Toe Ankle Boots in Beige Leather
$183.00
$595.00
ShopSimon
-12%
Free People
Womens Wisteria Ankle Boots In Taupe Gray
$174.00
$198.00
ShopSimon
-13%
Xti
Womens Ankle Booties In Taupe Gray
$111.00
$128.00
ShopSimon
-18%
Cushionaire
Womens Russel Knit Ankle Boot In Taupe Gray
$114.00
$139.00
ShopSimon
-12%
Naked Feet
Womens Xenus Platform Ankle Boots In Greige Gray
$157.00
$179.00
ShopSimon
-13%
Xti
Womens Ankle Booties In Taupe Gray
$111.00
$128.00
ShopSimon
-26%
Kaanas
Womens Porto Cowboy Booties In Beige
$196.00
$265.00
ShopSimon
-36%
Journee Collection
Collection Womens Tru Comfort Foam Lusinda Booties Gray
$69.99
$109.99
ShopSimon
-42%
Journee Collection
Collection Womens Tru Comfort Foam Hayven Booties Gray
$69.99
$119.99
ShopSimon
-19%
Kork-ease
Womens Skye Heeled Ankle Boot In Dark Red Pink
$157.00
$195.00
ShopSimon
-64%
Stuart Weitzman
Block-Heel Ankle Boots in Nude Leather Brown
$247.00
$694.00
ShopSimon
-11%
Kork-ease
Womens Shilo Ankle Booties In Taupe Brown
$205.00
$230.00
ShopSimon
-36%
Xti
Refresh Womens Fashion Italian Design Booties with Side Zipper by Xti Gray
$81.95
$128.19
ShopSimon
-49%
Esquivel
Jane Boot In Black Leather
$307.00
$598.00
ShopSimon
-77%
Stuart Weitzman
Block Heel Ankle Boots in Beige Suede
$177.00
$763.00
ShopSimon
-67%
L.k. Bennett
L. K.Bennett Arabella Suede Ankle Boot Brown
$213.98
$650.00
ShopSimon
-21%
Staud
Womens Hendrix Ankle Boots In Espresso Brown
$356.00
$450.00
ShopSimon
-25%
Chocolat Blu
Womens Gabby Wedge In Taupe Suede Brown
$198.00
$265.00
ShopSimon
-22%
Steve Madden
Harli Boots Womens Blush Square Toe Block Heel Booties Lion920 Beige
$109.00
$140.00
ShopSimon
-13%
Xti
Womens Ankle Booties In Beige
$111.00
$128.00
ShopSimon
-13%
Xti
Womens Ankle Booties In Beige
$111.00
$128.00
ShopSimon
-13%
Xti
Womens Ankle Booties In Beige
$111.00
$128.00
ShopSimon
-36%
Xti
Womens Suede Dress Booties In Medium Beige
$100.00
$156.00
ShopSimon
-14%
Xti
Womens Ankle Booties In Beige
$122.00
$142.00
ShopSimon
-13%
Xti
Womens Ankle Booties In Beige
$111.00
$128.00
ShopSimon
-4%
Xti
Womens 144464 Blocked Booties In Beige
$137.00
$142.00
ShopSimon
-13%
Xti
Womens Ankle Booties In Beige
$111.00
$128.00
ShopSimon
-13%
Xti
Womens Ankle Booties In Beige
$111.00
$128.00
ShopSimon
-36%
Xti
Womens Booties In Light/pastel Brown Beige
$100.00
$156.00
ShopSimon
-22%
Anne Klein
Moore Bootie Womens Sand Leather Block Heel Ankle Boots LION3 Gray
$109.65
$140.00
ShopSimon
-27%
Rockport
Womens Rockport Cobb Hill Laurel Rivet Boot US 6 Stone Nubuck Booties ZPO1795 Gray
$102.40
$140.00
ShopSimon
-69%
Ferragamo
Ferragamo Catania Ankle Stretch Boots in Black Suede
$288.00
$930.00
ShopSimon
-51%
Stuart Weitzman
Black Suede Ankle Boots
$327.00
$670.00
ShopSimon
-22%
Kork-ease
Womens Seeley Booties In Brown
$262.00
$338.00
ShopSimon
-50%
L.k. Bennett
Arabella Ankle Boots Brown
$325.00
$650.00
ShopSimon
-63%
Marc Fisher
Masina Heeled Bootie In Medium Natural Beige
$109.00
$297.00
ShopSimon
-63%
Stuart Weitzman
Coban Ankle Boots in Black Leather
$272.00
$728.00
ShopSimon
-59%
Stuart Weitzman
Maelie Ankle Booties in Black Leather
$254.00
$613.00
ShopSimon
-16%
Aquazzura
Black Mesh And Suede Pointed Toe Hot Stuff Ankle Booties
$317.00
$377.00
ShopSimon
-68%
Stuart Weitzman
Margot Ankle Boots in Black Suede
$206.00
$645.00
ShopSimon
-46%
Journee Collection
Collection Womens Tru Comfort Foam Wide Width Noralinn Booties Beige
$69.99
$129.99
ShopSimon
-23%
Kork-ease
Womens Kalista Leather Ankle Boot In Tan Brown
$222.00
$288.00
ShopSimon
-69%
Alexander Wang
Gabi Cutout Heel Ankle Boots in Black Leather
$288.00
$916.00
ShopSimon
-23%
Kork-ease
Womens Kalista Leather Ankle Boot In Black
$222.00
$288.00
ShopSimon
-39%
Loeffler Randall
Womens Marcella Woven Ankle Boots In Black
$336.00
$550.00
ShopSimon
Laurence Dacade
Black Suede Pete Studded Ankle Boots
$315.00
ShopSimon
-22%
Kork-ease
Womens Seeley Booties In Black
$262.00
$338.00
ShopSimon
-61%
Acne Studios
Cypress Con Ankle Boots in Brown Leather
$268.00
$683.00
ShopSimon
-26%
Homers
Sharon Heeled Ankle Boot In Crosta Negro Black
$339.00
$458.00
ShopSimon
-59%
Bueno
Womens Elliot Ankle Boots In Dark Wine Beige
$106.00
$259.00
ShopSimon
-65%
Ferragamo
Sal 85 Ankle Booties Brown
$439.99
$1,250.00
ShopSimon
-16%
Rag & Bone
Rag & Bone leather round toe chunky stacked heel western ankle boot Gray
$261.00
$310.50
ShopSimon
-73%
Sergio Rossi
Block Heel Ankle Boots in Black Leather
$278.00
$1,031.00
ShopSimon
-83%
Ferragamo
Zipped High-Heeled Ankle Boots in Black Leather
$237.00
$1,387.00
ShopSimon
-52%
BA&SH
Ba & Sh Block Heel Ankle Boots in Black Suede
$241.00
$507.00
ShopSimon
-36%
Xti
Refresh Womens Fashion Booties with Side Zipper by Xti Beige
$81.95
$128.19
ShopSimon
-36%
Xti
Womens Sport Booties By XTI Beige
$78.95
$124.00
ShopSimon
-34%
Xti
Womens Comfort Ankle Suede Booties By XTI Beige
$61.95
$94.00
ShopSimon
This season’s trends
- Dolce & Gabbana sandals
- Ecco sandals
- Gray Nike shorts
- Straw hats for men
- Prada sandals for women
- Swim trunks for women
- Moschino sandals
- Gucci shorts for men
- Gucci sandals
- Linen shirts for men
- Dr. Martens sandals
- Nike summer shoes for women
- Skechers summer shoes for women
- Clarks summer shoes for women
- HUGO BOSS sandals
- Cargo shorts for women
- Nike summer shoes for men
- Off-white sandals
- Skechers sandals
- Skechers sandals for women
- Lee shorts for women
- Amiri shorts
- Clarks sandals for women
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